I am carrying out the oxidation of benzylic methyl group to carbonyls. I wanted to use SeO2 and so wanted to know how many mole equivalents of it is required to oxidise one mole of methyl group. Is there any other procedure for the direct oxidation of this group with out converting to halides? Can SeO2 oxidize till the acid stage? If more than one equivalents is required then why? Is presence of water a must in the reaction.
Prasad,
According to balanced equation only one equivalent is needed, see
---http://library.sciencemadness.org/library/books/organic_reactions_v5.pdf#page=337
For experimental procedure, see
--- http://www.nrcresearchpress.com/doi/pdf/10.1139/v64-017
J. M. PEPPER and AITREYI SAHA, Canadian Journal of Chemistry. Volume 42 (1964)
You may use CuCl2/ DMF, see
--- European Journal of Medicinal Chemistry (2010), 45(10), 4479-4489
Good luck
One mole equivalents of selenium dioxide is required for oxidation of benzylic methyl group.
I would start with 1.5 equivalent slightly excess .In the real sense the stichiometry is different from balanced equation.This is due to side reaction of oxidizing agent with smaller molecules that are generated during the reactions.
I would use only 10 % more oxidating agent than the equivalent amount ... ei 1.1 moles.
Is potassiumdichromate too strong oxidating agemnt to this purpose. It can be used to prepare terephtalic acid from p-xylene.
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